Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
  • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
  • C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
  • A61P31/04—Antibacterial agents
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
  • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
  • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
  • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
  • C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
  • C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
  • C07C39/24—Halogenated derivatives
  • C07C39/42—Halogenated derivatives containing six-membered aromatic rings and other rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
  • C07C41/01—Preparation of ethers
  • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
  • C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2602/00—Systems containing two condensed rings
  • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
  • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Definitions

• R is a terpene radical chosen from the following group: ##STR3## OF EXO OR ENDO CONFIGURATION AND IN THE ORTHO, META OR PARA POSITION WITH RESPECT TO THE OH group.
• R 1 , r 2 may each be a hydrogen atom or halogen atom (Cl, Br, F, I) or a lower alkyl or lower alkoxy radical having a straight or branched chain of 1 to 4 carbon atoms or a nitro or cyano group.
• R is in the 2, 3 or 5 position of the phenol ring
• R 1 is a hydrogen atom or halogen atom, in particular C1 or Br, or a nitro, cyano group or a lower alkyl or lower alkoxy radical having 1 to 4 carbon atoms, in position 4 of the phenol ring.
• R 2 is a hydrogen atom or a lower alkyl radical of 1 to 4 carbon atoms.
• Demethylation may advantageously take place by means of red phosphorus in hydriodic acid.
• the characteristic absorption bands are as follows:
• No 2 1530, 1320, 870, 640
• aromatic nucleus 1625, 1580, 1490
• TMS tetramethyl silane
• nitric acid 1.42
• a solution cooled to 15° C, of 18.4g of O-isobornylphenol in 60 cm 3 of acetic acid.
• the temperature of the reaction mixture is maintained at 15° to 17° C for 5 hours and then the mixture is poured onto crushed ice. It progressively forms a red viscous mass which is extracted, after separation of the aqueous phase, with 350 cm 3 of ethyl ether.
• the ethereal solution is washed copiously with water then with 5% soda.
• the alkaline phase is acidified and extracted with ether. After evaporation of the solvent and crystallisation of the residue in petroleum ether (b.pt. 40°- 65°), 10.5g of brown product are obtained (m.pt. 180° - 182° C).
• aromatic nucleus 1620, 1590, 1485
• aromatic nucleus 1600, 1500, 890, 820
• aromatic nucleus 1620, 1590, 1500
• aromatic nucleus 1600, 1500, 820
• aromatic nucleus 1615, 1510, 860
• the spectrum comprises the following characteristic bands:
• norbornyl 2960, 2880, 14880 cm -1
• aromatic nucleus 1610, 1500, 815
• isocamphyl 2950, 2860, 1470, 1450, 1365, 1375 cm -1
• 8g of 85% m-perchlorobenzoic acid are added at ambient temperature and with stirring to a solution of 8g (0.03 mole) 3-isobornyl-4-methoxy benzaldehyde in 70 cm 3 anhydrous methylene chloride. After stirring for 2 hours, one filters and washes the organic phase with a solution of potassium bicarbonate, then with water. After drying, the solvent is evaporated and the residue is taken up in 50 cm 3 methanol and 5 cm 3 soda lye. One leaves it in contact for 30 minutes, then acidifies with HCl, dilutes with 200 cm 3 water and extracts with ether. The ethereal phase is washed with water and then the ether is driven off.
• the preceding product is heated with 90g pyridine hydrochloride for 6 hours to 220°-225° C.
• the mixture which is still hot is poured into 1 liter of water and the unsoluble substance formed is recovered by filtration. After washing with water and drying, one crystallizes from a benzene - iso-octane mixture (7:3) and 7.5g of pure product are thus obtained.
• M.P. 200° C.
• the preceding product is heated under nitrogen to 220° C for 4 hours with 56g pyridine hydrochloride.
• the mixture which is still hot, is poured into 300 cm 3 water.
• the insoluble matter is recovered by filtration, washed with water, dried and crystallized from a mixture of benzene and iso-octane (7:3) then from benzene. 2.1g of a pure product are obtained.
• M.P. 173° C.
• the bacteriostatic activity of the phenols according to the invention has been evaluated by the method of streaks in gelose media. This method comprises making increasing dilutions of the product to be tested, in nutritive geloses poured into a Petri dish.
• the various bacteria to be studied are then introduced onto the geloses in parallel streaks by means of a platinum loop which has been immersed in a 24 hour old culture of each bacteria.
• the bacteriostatic amount corresponds to the weakest concentration for which the bacteria does not develop along the striation.
• the following table shows the minimum inhibitory concentrations, expressed in mg/liter, of the products described in the examples.
• the LD 50 of the compounds of the invention, determined in the mouse and rat is greater than 1000 mg/kg.
• the products according to the invention may be used as anti-infectious agents.
• they may be made in a suitable form for oral or rectal administration, such as tablets, capsules, suppositories having a dose of 100 - 200 mg active ingredient to be administered at the rate of 200 mg - 1000 mg. per day.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Health & Medical Sciences (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• Animal Behavior & Ethology (AREA)
• General Chemical & Material Sciences (AREA)
• Medicinal Chemistry (AREA)
• Communicable Diseases (AREA)
• Pharmacology & Pharmacy (AREA)
• Life Sciences & Earth Sciences (AREA)
• Oncology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Cosmetics (AREA)

Priority Applications (1)

Applications Claiming Priority (2)

Related Child Applications (1)

Publications (1)

Family

ID=10071943

Family Applications (1)

Country Status (12)

Cited By (4)

Families Citing this family (2)

Citations (5)

• 1974
  • 1974-04-11 GB GB16142/74A patent/GB1510302A/en not_active Expired
• 1975
  • 1975-04-01 FR FR7510168A patent/FR2267093B1/fr not_active Expired
  • 1975-04-02 CH CH415575A patent/CH593221A5/xx not_active IP Right Cessation
  • 1975-04-02 CH CH415475A patent/CH593891A5/xx not_active IP Right Cessation
  • 1975-04-07 IE IE773/75A patent/IE40910B1/xx unknown
  • 1975-04-09 DE DE19752515382 patent/DE2515382A1/de not_active Withdrawn
  • 1975-04-09 US US05/566,364 patent/US4067899A/en not_active Expired - Lifetime
  • 1975-04-09 LU LU72249A patent/LU72249A1/xx unknown
  • 1975-04-09 LU LU72250A patent/LU72250A1/xx unknown
  • 1975-04-10 DK DK154175AA patent/DK142358B/da not_active IP Right Cessation
  • 1975-04-10 BE BE155288A patent/BE827797A/xx not_active IP Right Cessation
  • 1975-04-10 DK DK154075AA patent/DK142170B/da not_active IP Right Cessation
  • 1975-04-11 CA CA224,571A patent/CA1055529A/en not_active Expired
  • 1975-04-11 NL NL7504369A patent/NL7504369A/xx not_active Application Discontinuation
  • 1975-04-11 NL NL7504368A patent/NL7504368A/xx not_active Application Discontinuation
  • 1975-04-11 JP JP50043490A patent/JPS5830288B2/ja not_active Expired
  • 1975-04-11 JP JP50043491A patent/JPS5830289B2/ja not_active Expired
  • 1975-04-11 CA CA224,583A patent/CA1045164A/fr not_active Expired

Patent Citations (5)

Also Published As

Similar Documents